Dimethylformamide → HCID 66916104, compound

HRID 2061445Notes

Reaction equation

HRID 2061445 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]=[N:4][S:5]([C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16])(=[O:7])=[O:6].CN(C=O)C.[F:24][C:25]([F:29])([F:28])[CH2:26]I>>[CH3:1][N:2]([CH3:18])[CH:3]=[N:4][S:5]([C:8]1[C:13]([O:14][CH2:26][C:25]([F:29])([F:28])[F:24])=[CH:12][CH:11]=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16])(=[O:6])=[O:7]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 66915973HCID 66915973, compound

Product 1

HCID 66916104HCID 66916104, compound

Procedure

To a solution of N-(1-dimethylamino-methylidene)-2-nitro-6-hydroxy-benzenesulfonamide (847 mg, 3.1 mmol) in DMF (10 mL) NaH (135 mg, 55% dispersion in Nujol, 3.1 mmol) is added under argon. After stirring for 15 min 2,2,2-trifluoro-ethyl iodide (2777 mg, 12.4 mmol) is added, and stirring is continued for 20 h. Volatiles are evaporated under reduced pressure, and the residue is partitioned between EtOAc and water. The organic phase is washed with saturated brine, dried (Na2SO4) and evaporated. Chromatography of the residue (silica gel, hexanes/EtOAc/acetone 2:1:3) gives N-(1-dimethylamino-methylidene)-2-nitro-6-(2,2,2-trifluoro-ethoxy)-benzenesulfonamide.

Workup

  1. additionis added
  2. customVolatiles are evaporated under reduced pressure
  3. customthe residue is partitioned between EtOAc and water
  4. washThe organic phase is washed with saturated brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-3ae055e85c2f4bfab820a354b235faca
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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